An investigation into reactivity and selectivity in cycloadditions of 1,3-dipoles with formamidines

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dc.check.opt-outNoen
dc.check.reasonReleasing this thesis would cause substantial prejudice to the commercial interests of University College Corken
dc.contributor.advisorMcCarthy, Daniel G.en
dc.contributor.authorBrennan, Tina-Marie
dc.contributor.funderCork City Councilen
dc.date.accessioned2015-12-03T12:05:11Z
dc.date.issued2015
dc.date.submitted2015
dc.description.abstractThe objective of this research was to investigate the synthesis of nitrile oxides and to study their reactivity in 1,3-dipolar cycloadditions with formamidines. Chapter one looks at the literature surrounding the 1,3-dipolar cycloaddition reaction. It explores the generation of 1,3-dipoles (mainly nitrile oxides) and dipolarophiles (predominantly amidines). It discusses the potential synthetic uses of the 1,3-dipolar cycloadducts. It examines both and inter- and intra-molecular cycloaddition reactions. It recognises the use of the 1,3-dipolar cycloadditions as a successful method in building natural products and oxadiazolines. The decomposition of oxadiazolines as a route to nitriles is also outlined in this chapter. Chapter two discusses the results of this research candidate. The preparation of nitrile oxide precursors - hydroximoyl halides - is outlined at first. The generation of nitrile oxides is then demonstrated, followed by the preparation of furoxans. Methods for preparing the reference materials (nitriles and ureas), which result from decomposition of oxadiazolines, then follow. The preparation of series of Δ2-1,2,4- oxadiazolines via the 1,3-dipolar cycloaddition reaction is illustrated in this chapter. The selectivity of the addition of nitrile oxides to dipolarophiles was tested by competition reactions, which are also described in this chapter. NMR techniques were used in the study of the kinetics of the 1,3-dipolar cycloadditions used for the preparation of a series of Δ2-1,2,4-oxadiazolines, which is addressed in this chapter. Chapter three charts the experimental procedures followed to gain results which are discussed in chapter two. It also outlines all analytical data produced during the course of this research.en
dc.description.statusNot peer revieweden
dc.description.versionAccepted Version
dc.format.mimetypeapplication/pdfen
dc.identifier.citationBrennan, T.-M. 2015. An investigation into reactivity and selectivity in cycloadditions of 1,3-dipoles with formamidines. PhD Thesis, University College Cork.en
dc.identifier.endpage380
dc.identifier.urihttps://hdl.handle.net/10468/2123
dc.language.isoenen
dc.publisherUniversity College Corken
dc.rights© 2015, Tina-Marie Brennan.en
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/en
dc.subjectOxadiazolineen
dc.subject1,3-dipolar cycloadditionen
dc.subjectNitrile oxideen
dc.subjectAmidineen
dc.thesis.opt-outfalse
dc.titleAn investigation into reactivity and selectivity in cycloadditions of 1,3-dipoles with formamidinesen
dc.typeDoctoral thesisen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD (Science)en
ucc.workflow.supervisord.mccarthy@ucc.ie
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